Vacation Rentals in Fairfield, CT

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Fairfield, CT holiday rentals
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355 Holiday rentals and Airbnb in Fairfield, CT

Best family friendly Fairfield, CT holiday rentals

Among the 355 accommodations in Fairfield, CT, here are the 4 best family friendly rentals

Southport Shoreline Charm: Elegant Coastal Escape - Fairfield, CT
8.8 5 reviews

Southport Shoreline Charm: Elegant Coastal Escape

apartment, Fairfield
This three-bedroom flat is conveniently located in Southport, Fairfield, just a short 5-minute drive from the beaches and a few minutes from the town centre. The surrounding area offers a range of shops, restaurants, and attractions, making it an ideal base for exploring the local area.
The property features a spacious living area, dining room, and a cosy back room with a large flat-screen TV. It can comfortably accommodate up to seven guests. The apartment is fully equipped with everything you need for a comfortable stay, including a kitchen with a dishwasher, a washing machine, and a dryer, plus a ping pong table in the basement for entertainment.
The Colonial Cottage At Fairfield Beach - Fairfield, CT
10 4 reviews

The Colonial Cottage At Fairfield Beach

house, Fairfield
This historic Fairfield Beach cottage offers a prime location, just 800 metres from Jennings Beach and a short distance from downtown Fairfield.
This two-bedroom, one-bathroom property accommodates up to four guests and includes essential amenities like internet, a kitchen, and air conditioning, making it suitable for families and business travellers.
The Elijah Sterling House - Fairfield, CT
10 66 reviews

The Elijah Sterling House

apartment, Trumbull
This three-bedroom apartment is situated in Trumbull, Connecticut, a 10-minute drive from the Total Mortgage Arena and the Bridgeport Amphitheatre.
The apartment, housed in the historic Elijah Sterling House, dating back to 1791, offers a fully equipped kitchen, a spacious outdoor patio, and multiple living areas, accommodating up to seven guests.
Southport Shoreline Charm: Elegant Coastal Escape - Fairfield, CT
9.6 144 reviews

Southport Shoreline Charm: Elegant Coastal Escape

apartment, Fairfield
This 3-bedroom house in Fairfield is located just a short distance from the town centre and a 5-minute drive from the beach. It has received excellent ratings for cleanliness, location, and overall experience.
The house spans 9 square metres and comfortably accommodates up to 7 guests. It includes a fully equipped kitchen, a spacious living area, a private garden, and a range of amenities for a comfortable and enjoyable stay, including a ping pong table, sound machines in each bedroom, and a work-from-home friendly setup.

Best Fairfield, CT holiday rentals with a pool

Among the 355 accommodations in Fairfield, CT, here are the 4 best rentals with a pool

Quaint Private Two Bdrm With Balcony, Stream View! - Fairfield, CT
9.3 15 reviews

Quaint Private Two Bdrm With Balcony, Stream View!

apartment, Bridgeport
This two-bedroom flat in Bridgeport offers convenient access, being just a 4-minute drive from Sacred Heart University.
This Airbnb provides high-speed WiFi, a fully equipped kitchen, and a private balcony, comfortably accommodating up to five guests with new Serta Sleeper mattresses.
Spacious Cottage Loft - Fairfield, CT
10 111 reviews

Spacious Cottage Loft

apartment, Bridgeport
The Spacious Cottage Loft is located in Black Rock, a charming seaside neighbourhood in Bridgeport, Connecticut, set on the grounds of a historic Victorian house dating back to the 1840s. The cottage has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
The cottage has one bedroom and one bathroom, comfortably accommodating two guests. It offers a range of amenities including a fully equipped kitchen, two smart TVs, a dedicated workspace, a private patio, and access to a swimming pool during the warmer months.
Modern Artist Retreat Near Beach - Fairfield, CT
9.3 47 reviews

Modern Artist Retreat Near Beach

apartment, Fairfield
This Fairfield apartment is conveniently located just a short walk from the beach, shops, historical sites, and a wide selection of restaurants. With excellent user, location, and cleanliness ratings, this property offers a comfortable and enjoyable stay.
The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, air conditioning, a private garden, a swimming pool, a jacuzzi bath, and a separate in-law suite option available for an extra fee.
Sunny Modern 3 Bedroom House Walk To  Beach And Town - Fairfield, CT
No reviews

Sunny Modern 3 Bedroom House Walk To Beach And Town

apartment, Fairfield
This three-bedroom flat is located in Downtown Fairfield, a 14-minute walk from the Fairfield Museum and History Centre and a 10-minute walk from South Benson Marina.
This apartment offers accommodation for six guests with air conditioning, a hot tub, on-site laundry facilities, and essential toiletries.

Frequently asked questions about holiday rentals in Fairfield, CT

  • What are the must-see sights in Fairfield, Connecticut?

    Fairfield boasts a lovely mix of historical sites and natural beauty. You definitely want to check out the Fairfield Museum and History Center to learn about the town's rich past. Lake Mohegan is gorgeous for a stroll or picnic, and the charming downtown area offers plenty of boutique shopping and places to grab a bite to eat. The historic Old Town Hall is also worth a visit.
  • What are the best Airbnb and holiday rentals in Fairfield, CT?

    The Inn At Fairfield Beach, Southport - Ct Across From Beach and Cozy Home Away From Home are the most popular Airbnb and holiday rentals in Fairfield, CT among travellers.

  • Are there any unique natural phenomena in Fairfield, Connecticut?

    Fairfield doesn't have any dramatic, unique natural phenomena like geysers or massive caves. However, its location on Long Island Sound provides beautiful coastal scenery, and the diverse ecosystems within Lake Mohegan and the surrounding areas offer opportunities for birdwatching and nature walks. The beaches are also a key attraction.
  • What are the most popular Airbnbs in Fairfield, CT?

  • What essentials should you bring along to Fairfield, Connecticut?

    Pack comfortable walking shoes, as you'll likely be doing a lot of exploring on foot. Depending on the time of year, bring layers of clothing as the weather can be unpredictable. Sunscreen and insect repellent are always good ideas, especially during the warmer months. Don't forget your swimwear if you plan on hitting the beach!
  • What are the best holiday rentals with a pool in Fairfield, CT?

  • What famous events or festivals are happening in Fairfield, Connecticut?

    Fairfield hosts various local events throughout the year. Information on specific dates and events is best found closer to your travel dates by checking the town's official website or local event listings. There isn't one single, nationally renowned festival that defines Fairfield.
  • What are the best rentals for families and kids in Fairfield, CT?

  • Where can you find the best restaurants serving local dishes in Fairfield, Connecticut, and what are the must-try specialties?

    Fairfield has a diverse culinary scene. For fresh seafood, try one of the restaurants along the coast. There are also many excellent Italian restaurants reflecting the area's heritage. Specific restaurant recommendations change frequently, so checking local reviews closer to your visit is recommended. There isn't one single 'must-try' Fairfield specialty, but the emphasis is on fresh, local ingredients.
  • What are the best rentals or Airbnbs with a jacuzzi in Fairfield, CT?

  • What are some less-famous attractions in Fairfield, Connecticut that are worth a visit?

    The Pequotsepos Nature Center offers lovely nature trails and educational exhibits. Exploring the various smaller parks and beaches scattered throughout town can also be a rewarding experience. Many of Fairfield's residential areas have beautiful architecture and charming streets to wander.
  • What are the best activities for engaging with locals and understanding their culture in Fairfield, Connecticut?

    Visiting local farmers' markets is a great way to interact with residents and sample local produce. Attending community events or local festivals (check local listings for schedules) can also provide opportunities to meet people. Simply striking up conversations with people in local shops or cafes is another way to experience the local culture.
  • What unique natural landscapes and terrain features can travellers explore in Fairfield, Connecticut?

    Fairfield's landscape is characterised by its coastal location, with beaches and the Long Island Sound. Inland, you'll find rolling hills, wetlands, and several smaller lakes and ponds, including Lake Mohegan. The terrain is generally fairly flat, making it easy to explore on foot or by bicycle.
  • How many days are ideal for a visit to Fairfield, Connecticut, and what are some itinerary suggestions?

    Two to three days is a good amount of time to explore Fairfield's main attractions. A possible itinerary could include: Day 1: Explore downtown, visit the Fairfield Museum and History Center, enjoy a meal by the water. Day 2: Spend time at Lake Mohegan, relax on the beach, and explore one of the smaller parks. Day 3: Visit the Pequotsepos Nature Center and perhaps take a scenic drive along the coast.

Nearby regions

Best Fairfield, CT holiday rentals with a balcony

Beechmont-charming Colonial For Events And Getaways! - Fairfield, CT
8.0 1 review

Beechmont-charming Colonial For Events And Getaways!

house, Bridgeport
This Bridgeport property, a colonial-style house, is located 13.7km from Silver Sands State Park and 19.3km from the Connecticut Post Mall, offering convenient access to local attractions.
The 307 square metre dwelling boasts one bedroom, four bathrooms, and accommodates up to 23 guests, featuring a fully equipped kitchen, free Wi-Fi, private parking, and a terrace/garden.
Zen, Spacious & Comfy 2 Bed, Lux Beds - Fairfield, CT
10 2 reviews

Zen, Spacious & Comfy 2 Bed, Lux Beds

apartment, Bridgeport
This two-bedroom basement flat is situated in Bridgeport's Brooklawn-St. Vincent neighbourhood, conveniently close to Sacred Heart University and Bridgeport Hospital.
The 2-bedroom property sleeps 5, boasts high-speed internet, a washer/dryer, and a fully equipped kitchen, plus access to a large yard with a swing; nearby attractions include the Bridgeport Downtown South Historic District and Fairchild Wheeler Golf Course.
Charming Colonial For Events!  Perfect For Family Reunions And Group Getaways! - Fairfield, CT
8.8 10 reviews

Charming Colonial For Events! Perfect For Family Reunions And Group Getaways!

apartment, Bridgeport
This six-bedroom, four-bathroom house, situated in Bridgeport's Downtown South Historic District near Perry House, offers easy access to attractions such as Beardsley Zoo and the Bridgeport Bluefish Baseball Club (distances not specified).
The 3,300 sq ft (approximately 307 sq m) property sleeps 8-12 guests and includes a modern master suite with a private terrace, a den, stainless steel appliances, off-street parking for six cars, and extensive outdoor space including a half-acre lawn.
Villa Après Sea - Fairfield, CT
9.0 1 review

Villa Après Sea

house, Westport
This Westport holiday home offers exclusive private access to Compo Beach, located 27 kilometres from Silver Sands State Park and 32 kilometres from Connecticut Post Mall.
This spacious, air-conditioned detached house covers 305 square metres, accommodating up to 11 guests with four bathrooms, a fully equipped kitchen, complimentary Wi-Fi, and free private parking.

Best Fairfield, CT holiday rentals with parking

Fairfield! 5 Bedroom, 3.5 Bath On Cul-de-sac - Fairfield, CT
10 52 reviews

Fairfield! 5 Bedroom, 3.5 Bath On Cul-de-sac

apartment, Fairfield
This spacious, renovated apartment in Fairfield is conveniently located just a short distance from the town centre, universities, and transportation to NYC Grand Central. The apartment boasts excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The apartment has 5 bedrooms and 3 bathrooms, comfortably accommodating up to 12 guests. Amenities include a private heated pool, a well-equipped kitchen, a spacious living area, a family room with a large TV, and a fully furnished garden with outdoor furniture.
Spacious Studio With Pool Table - Fairfield, CT
8.6 7 reviews

Spacious Studio With Pool Table

studio, Westport
This Westport studio apartment is centrally located, a short drive (approximately 0.8km) from Westport town centre, 1.1km from Compo Beach, and 0.6km from the Westport Country Playhouse.
The 107-square-metre self-contained apartment sleeps four, features a fully equipped kitchenette with microwave, a private entrance, on-site parking for two cars, and amenities including a pool table, iMac, and home theatre system.
The Creekside Cottage - Fairfield, CT
9.9 52 reviews

The Creekside Cottage

house, Fairfield
Creekside Cottage, a Fairfield Beach dwelling, is a one-minute walk from Fairfield Beach and close to Fairfield town centre and its restaurants.
This self-catering property offers one bedroom, one bathroom, sleeps two, includes parking, internet, air conditioning, a garden, and a patio; guests can enjoy nearby attractions such as Jennings Beach and the Fairfield Museum & History Centre.
Walkable Beach Home W/ Bikes & Bonfire - Fairfield, CT
10 8 reviews

Walkable Beach Home W/ Bikes & Bonfire

apartment, Fairfield
This Fairfield apartment is a short walk from both the beach and the town centre, making it ideal for exploring the area. It has excellent ratings for location, cleanliness and overall experience.
The property has two bedrooms and a bathroom, plus a third room that can be used as an extra bedroom, making it suitable for groups of up to five guests. You'll find everything you need for a comfortable stay, including a fully equipped kitchen, outdoor space with a barbecue and fire pit, and even paddle boards for exploring the water.
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